In August of 1999 I joined a small startup that was intent on changing education using the power of the Internet. My colleagues and I did it. It has been incredibly fun, challenging, full of highs and lows and ultimately satisfying. I got to write and design products used by millions of people. I traveled the world, met thousands of people, saw some amazing things and heard incredible stories. I want to sincerely thank every one of you who made that possible.

What’s Next

Some of you might be wondering what’s next for me. I have no comment at this time. If my life is a reality TV series I’m going to end this season on a cliff hanger.

This last week I had a chance to sit down with some seniors at GWU and talk about my experience in the exciting world of software startups. It was a fun experience and gave me a chance to reflect on my 18 years working on web and Internet based software projects. Here are a few of the observations I shared with the class:

The Job You Want Doesn’t Exist. You Have to Create it.

Every year Forbes Magazine publishes a list of jobs that didn’t exist a decade ago. If you are really planning to change the world with your ideas and technology be prepared for the fact that your job doesn’t exist. You will need to invent it. In fact you are going to have to invent a bunch of other jobs to make the business and its ecosystem emerge.

In 1995 when I graduated from college the Internet was just beginning to be a thing. I ended up getting a job as a webmaster. This was 1995. The web hadn’t even existed when I started my studies in 1991. As I started my career, this technology wave was rising. A series of lucky events placed me in the right place to catch this wave. I graduated and got a job as a “webmaster”. I’ve learned to look for these waves and that if you make yourself ready you can catch it.

The job you want on that coming wave doesn’t exist yet. When you first start doing it, people will say, “WTF?” When I told my roommate about my job as a “webmaster” he joked, “webmaster? what are you spiderman?”

You are Going Continuously Fail and Suck

I don’t mean in the baseball way where you get so many at bats but you’re a champion if you get on base 30% of the time. I don’t mean it like the classic Edison quote, “I haven’t failed, I’ve just figured out 10,000 ways it doesn’t work.” I want you to have the expectation that it isn’t going to work period. You are going to pretty much spend every day alternating between totally failing and just merely sucking at what you are trying to do. Your life will be a series of broken builds, bugs, things that were really great in theory but users hated. Eventually out of all these failures something beautiful might emerge. That failure might even become a runaway success. Even so, in ten years you are going to look back and say, “wow that was terrible.”

This point was better said in this Helpful PSA Entitled: Point/Counter-Point Should I Get a Tattoo.

Encourage Plain Speaking and Criticism

It is really hard to hear how terrible your idea is or tell a team member their idea is terrible. Even though almost every idea is terrible in one way or another. It is very easy to stand around smiling and nodding, but that really doesn’t help. When you do that terrible ideas live on. They are never forced to evolve. Worse, critics start talking behind the backs of the leader of the initiative. A terrible idea ends up moving forward but is undermined by the organization. The result of this is usually something worse than the terrible idea itself. You don’t have to be mean about it. You have to set the expectation with your team that most ideas are probably going to be pretty terrible. If an idea isn’t terrible when it is first pitched then you probably didn’t spot how terrible the idea was.
It requires a bit of a thick skin to stand up there and hear about how terrible your ideas are. Hopefully some of the critics will have helpful suggestions such as “never speak of this again” or “that might be cool if…” Don’t let those criticism over whelm you. Keep trying. Come up with other ideas, or revisit the idea a bit differently. Keep pushing and prototyping until something useful emerges from that brain of yours.

Don’t be a Jerk Every Day

Some say I still need to learn this lesson. When you speak plainly and recognize how terrible the thing you are working on is, it becomes very easy to become a gruff and nasty person to your fellow human beings. This is something to be avoided. Keep your criticisms to the writers room. Find time to reach out and bring snacks for the team. Recognize the few moments of success where even though it will likely blow up again soon; things are actually going well. Every person is going to have a different level of tolerance and general stubbornness. It is your job as a fellow human being to recognize how hard you have to push and push no harder.

Lead by Establishing a Common Purpose, Drive People Towards Mastery and Reward Autonomy

I believe that big breakthroughs usually come from small, super motivated, agile teams. Dan Pink has a great Ted Talk on the core concepts of Autonomy, Mastery and Purpose. It is very easy to break your team’s spirit. As a manager and the visionary one can easily fall into the trap of “I have this huge vision and a list of a thousand things for you to do, now go do it people.” The first thing you have to realize is that your vision is wrong. There are a few useful things in there, but seriously your idea will fail. Even if the developers manage to meet the impossible schedule, divine all of your hidden features and get everything exactly as you wanted it the first time.

If you really want to make amazing things with your small team. You have to push your team to deeply understand the customers and the overall purpose of what you want to accomplish. Then you need to encourage and reward initiative that drives towards that result. Keep your team focused on the purpose, on the broader cause. Don’t let them get too bogged down in requirements and mockups.

The Advice About “When to Ship” Is Probably Wrong

You will often hear that you need to ship early and often to customers. There is a lot of value in getting feedback from customers. Still this can be bad advice. It really depends on how your users perceive you and how you are going to manage the impact of the changes you’re making. If you throw a bunch of change at the users on a continuous basis they will go find something more stable. Change takes time for the users to absorb. You have to understand the amount of change your users can accommodate and then go no faster.

Don’t Cram Your Releases

It is always tempting to try to fill up the release with millions of new ideas and concepts. You probably have a list of things your users want and it always feels great to check them off the list. However in keeping with the last point, know that your users can only understand a few new things at a time. My favorite example of this is the launch of the iPad. All the other tablet makers lined up at CES before Apple announced it’s tablet and tried to create their own. Sprint had one that had a bendable screen. Microsoft and HP had one that opened into two screens like a book. Everyone was wondering what the iPad was going to be and there was universal derision in the tech press when it turned out to basically be a really bigger version of the iTouch. It turned out though that this was really a smart move. They made on major change (size) and left out things like a camera until users had made the leap. It would have been easy for apple to cram a bunch of other things into the iPad 1, but they didn’t. A release is a little like telling a story. If your story is too long, no one reads it. If you build a bunch of functionality that users never know about; then all that effort was wasted.

Continuously Invest in Things that Hook Your Users and/or Your Users Have to Do

You need to measure every page your the app or website. What things are your users doing often, whats their experience and how can you improve it. The team I managed working on CourseSites was always looking at the signup page. How long did a signup take. Could you easily find your institution. We wanted to grow usage of the site, so that meant we had to continuously invest in that page. Every release it gets tweaked and improved. We set goals to improve the accuracy of the data capture, and reduce dropouts.

If you don’t know how you users are using the product and you don’t know what hooked them; then it is impossible to manage the product over the long term. It is very easy to get caught up in making some flashy new capability based on some latest market buzz, but if that leads to neglect of a critical feature then you are going to suffer in the marketplace. You also need to understand that usage will shift over time. Things that were compelling a few years ago, will be dead on your site tomorrow.

Maintenance Will Be Most of Your Job

Of the course of a successful software product’s lifespan something like 90% of the effort goes into maintenance, not new functionality. Before the product goes into widespread usage you will get an opportunity to explore and innovate tons of new capabilities. Once it gets adoption, your users are going to demand continuous improvement. They may even resent totally new features because they will see it as taking away from expanding the things they like to do. Maintenance gets kind of a bad rap. People mistake maintenance for a lack of innovation. Well managed maintenance is continuously optimizing things. It is speeding up transactions, improving reliability and polish, and simplifying workflows. Consider Google search. We don’t need a totally new user interface for Google. We just need it to constantly stay on top of the changing set of information on the internet and give us the best results. Microsoft tried some really innovative things in launching Bing!. Automatic product recommendations, health advice, travel stuff. They even marketed it as a “decision engine”, not just search. However ultimately it has struggled, because those features were not the core feature and are not compelling enough to draw a user away from Google. Google has worked to maintain a slight edge on search results through regular maintenance.

Closing Point

If you take anything away from this essay try to remember this. There are terrible things that are useful and things that are just terrible. If you are able to make something useful into something slightly less terrible then the world is yours.

I’m pretty sure that my readers will agree that libraries are worth saving in spite of the technology advances in the past few years. In the interest of brevity I will skip the several page rant about the importance of libraries as cultural institutions and the unique discovery process of browsing the stacks or collections assembled by a curator. Let us presume that if you don’t like libraries, we can hash it out in the comment section or you can just skip this weeks installment.

On June 10th my neighbors and I got a nasty surprise. Our local library branch was being “relocated” outside our walking zone. A single public meeting would be held on June 16th at the old library location to inform us about the relocation, with the county board expected to approve the motion in the following month. This did not leave us much time to act or organize. Perhaps in another era our library would have slipped away from us like the Washington Senators all those years ago.

Yet those who might have sought to slip this through were in for a surprise. The surrounding neighborhoods are vibrant and alive with strong social networks. Neighbors still know each other and with the aid of Yahoo Groups and Facebook and old fashioned fliers the word was quickly spread to come and save the library.

A nearby resident I have yet to meet in person sent out a call for people to send out fliers. I volunteered and was sent a word document to print. I went online and ordered 200 copies and arrived an hour later for in store pickup. I got a few fliers out before I had to leave town for the Sakai 2010 conference, but my wife graciously took up the charge and took the kids door to door. Residents in other surrounding neighborhoods did the same organized on routes by this one activist. I personally started a Facebook Group and quickly saw it grow and neighbors posted update after update. People reported their conversations with officials and staff. The PTA was contacted along with other organizations.

The evening of the 16th arrived. I tried to get home from Denver to boost the crowd size since this was our only chance. My wife got a sitter and walked over to the library. To her dismay the parking lot was nearly empty. She walked into the library disheartened that all this work had not resulted in turnout. However when she opened the doors, she saw it was standing room only. Just like her the neighbors had walked to the library. Of the 400+ people in attendance 80% or more had chosen to walk to the library rather than drive.

The County Manager and Director of the Library were also in for a suprise as attempted to sell us on their new vision of a library. Neighbor after neighbor stood up and spoke out against the concept. Arguments developed on forums, facebook and listservs were articulated. The 5th grade president of the local elementary school student body spoke eloquently how he used the library after school with his friends every day.

The meeting ended with the manager choosing to delay the final decision. So we continued to organize. Word of the meeting turnout spread through the community and pictures were posted online. Research was done using the library and online to determine legal and other options. Maps of the impact to the neighborhood were shared to demonstrate how we’d be affected by the change. More talking points were developed and detailed community impact statement was put together by many contributors in the community. We constructed knowledge from local history projects and old timers reflections to show the community’s long support for the library. Old timers told us how the library had moved to its current location in 1973, after being located only 2 blocks away before that and had originally been built with neighborhood, not county funds in the 1930s. The elaboration of community history and construction of knowledge using various “DIY U” style tools was impressive. The ability of the community to educate itself and eachother about the value of libraries and impacts of removal was equally astounding.

A few things I learned: Libraries contribute to a walk score. The more walkable your neighborhood the higher your property values. Typically one point on the walk score can be worth 2-4K dollars in my area. In losing the library it seemed we might drop 5-10 points which would be significant to property values already depressed by the housing collapse. The LEED scoring system for commercial offices includes 20 items, one of which is a library within .5 miles of your office space. This would have meant affected the ability of two nearby office complexes to get a high LEED score (something which they were touting in their rental materials). These are just a few facts and if you are trying to save your local library feel free to reuse them.

The result was today Friday the 18th, 8 days after it began the county manager was forced to announce that the library was staying right where it was. The ability of local residents to connect and communicate online worked in combination with our walkable streets and community spirit to create the perfect storm. I’m told that usually community activism takes months and had expectations that our campaign to save the library would draw out for a long time based on the comments from others who’d worked on other community zoning and services issues. In a way the community center project did what it set out to do in a most unexpected way, it built community. By the way the community center (sans library) is still being built for residents down the road. Since they already have 2 walkable libraries and were just as surprised about this move as we were; everybody wins.